WO2021254751A1 - Utilisation de composés d'indole pour traiter les signes du vieillissement de la peau - Google Patents

Utilisation de composés d'indole pour traiter les signes du vieillissement de la peau Download PDF

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Publication number
WO2021254751A1
WO2021254751A1 PCT/EP2021/064082 EP2021064082W WO2021254751A1 WO 2021254751 A1 WO2021254751 A1 WO 2021254751A1 EP 2021064082 W EP2021064082 W EP 2021064082W WO 2021254751 A1 WO2021254751 A1 WO 2021254751A1
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WO
WIPO (PCT)
Prior art keywords
skin
acid
cells
indole compounds
oil
Prior art date
Application number
PCT/EP2021/064082
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English (en)
Inventor
Cleo Lucinda BISHOP
David Andrew Gunn
Bijan Harichian
Gail Jenkins
Deborah Anne MILLIGAN
Jose Guillermo Rosa
Eleanor Jane TYLER
Linda Jane Wainwright
Original Assignee
Unilever Ip Holdings B.V.
Unilever Global Ip Limited
Conopco, Inc., D/B/A Unilever
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Unilever Ip Holdings B.V., Unilever Global Ip Limited, Conopco, Inc., D/B/A Unilever filed Critical Unilever Ip Holdings B.V.
Priority to EP21728239.1A priority Critical patent/EP4168130A1/fr
Publication of WO2021254751A1 publication Critical patent/WO2021254751A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol

Definitions

  • the present invention relates to the use of indole compounds for treating signs of skin aging.
  • Skin aging is a complex process, and alterations in human skin due to aging have distinct characteristics as compared to other organs. Characteristics of intrinsic or chronological skin aging include dryness, visible fine lines and wrinkles, uneven skin pigmentation, loss of elasticity and skin sagging. Extrinsic factors including exposure to sunlight, pollutants and cigarette smoke can accelerate the skin aging process, especially on the face.
  • the present invention provides the use of one or more indole compounds corresponding to general formula (I):
  • the invention also provides the use of one or more indole compounds of general formula (I) as defined above in, and for the manufacture of, topical compositions for treating signs of skin aging.
  • the invention also provides one or more indole compounds of general formula (I) as defined above for use in the selective elimination of senescent skin cells.
  • the invention also provides the use of one or more indole compounds of general formula (I) as defined above in, and for the manufacture of, topical compositions for the selective elimination of senescent skin cells.
  • the invention also provides a cosmetic method for treating signs of skin aging, comprising topically applying to the skin a cosmetic composition containing one or more indole compounds of general formula (I) as defined above.
  • cosmetic refers to a treatment which does not cure, treat or prevent a disease or disorder, but instead serves as a skincare product or to modify or improve the appearance of the skin, e.g. the colour, texture or moisture content of the skin.
  • Z in formula (I) is generally selected from linear or branched, saturated or unsaturated alkylene or hydroxyalkylene groups having from 1 to 10 carbon atoms.
  • Z in formula (I) is selected from linear saturated alkylene or hydroxyalkylene groups having from 1 to 4 carbon atoms such as methylene, ethylene, propylene, butylene, hydroxyethylene, hydroxypropylene and hydroxybutylene and mixtures thereof. More preferably, Z in formula (I) is methylene.
  • M in formula (I) is generally selected from hydrogen or a salt-forming cation selected from alkali metal (e.g. sodium, potassium, lithium), divalent metal (e.g. calcium, magnesium, zinc), ammonium, C1-C4 substituted ammonium and C1-C4 alkanolamine and mixtures thereof.
  • alkali metal e.g. sodium, potassium, lithium
  • divalent metal e.g. calcium, magnesium, zinc
  • ammonium C1-C4 substituted ammonium and C1-C4 alkanolamine and mixtures thereof.
  • M in formula (I) is selected from hydrogen, sodium and potassium and mixtures thereof. More preferably, M in formula (I) is hydrogen.
  • the one or more indole compounds of general formula (I) are used for treating signs of skin aging.
  • the term “treating” denotes reducing, preventing or eliminating.
  • the expression “signs of skin aging” denotes one or more characteristics of intrinsic or chronological aging such as thin and dry skin, fine wrinkles, decreased elasticity and aberrant pigmentation. These signs affect everyone, whatever their skin type or state of health. As noted above, the process may be amplified by extrinsic factors such as exposure to sunlight, pollutants and cigarette smoke.
  • Signs of skin aging can be measured using clinical and biophysical methods. Functional parameters like skin surface pH, stratum corneum hydration (SCH) or transepidermal water loss (TEWL) are for instance applied as markers of the status and integrity of the skin barrier. During aging, skin surface pH may increase, whereas TEWL decreases. Structural assessments such as skin microtopography and Cutometer® measurements may be used to measure surface roughness and skin elasticity respectively. During aging, surface roughness may increase, whereas skin elasticity decreases. Age-dependent skin colour changes, such as the degree of luminance and yellowness in the skin tone, may be measured using spectrophotometry and expressed as L*and b* respectively in the CIE L*a* b* colour space.
  • the one or more indole compounds of general formula (I) are used in the selective elimination of senescent skin cells.
  • the term “senescent” refers to a state of permanent cell cycle arrest in which cells remain metabolically active and adopt characteristic phenotypic changes. The establishment of this phenotype is believed to be either the result of telomere shortening after several cell divisions (replicative senescence) or a response to stress stimuli (stress-induced senescence).
  • telomere shortening after several cell divisions (replicative senescence) or a response to stress stimuli (stress-induced senescence).
  • stress-induced senescence One of the defining features of senescent cells is their stable cell cycle arrest. This cell cycle exit is controlled by activation of the p53/p21 GIP1 and p16' NK4a /Rb tumour suppressor pathways.
  • senescent cells are nonresponsive to mitogenic or growth factor stimuli; thus, they are unable to reenter the cell cycle even in advantageous growth conditions.
  • Senescent cells are also distinct from terminally differentiated cells, which are also irreversibly withdrawn from cell cycle. While terminal differentiation is the result of a defined developmental programme, which turns undifferentiated precursors into specialized effector cells, senescence is mainly implemented as a cellular stress response.
  • Senescent cells can be identified in vitro and in vivo, since they display a number of characteristics that allow their identification.
  • senescent cells often appear multinucleated, large and extended, and exhibit spindle and vacuolisation features. They also display modifications in the organisation of chromatin that can help identify them. In normal cells, DNA staining reveals completely uniform colour outlines, whereas senescent cells usually show dot-like patterns, known as senescence-associated heterochromatic foci (SAHF). This phenomenon is due to intensive remodelling in the chromatin, which results in less susceptibility for digestion by nucleases.
  • SAHF senescence-associated heterochromatic foci
  • SASP senescence-associated secretory phenotype
  • a distinctive measurable feature of senescent cells is the presence of b-galactosidase enzymatic activity.
  • This enzyme normally displays activity at pH 4.0 within lysosomes, but in senescent cells it is also active at pH 6.0.
  • This phenomenon is termed senescence associated ⁇ -galactosidase (SA ⁇ -gal) activity and is thought to be due to an enlargement in the structure of lysosomes in senescent cells.
  • SA ⁇ -gal activity is detectable by histochemical staining by using X-gal as a substrate for SA ⁇ -gal. Since SA ⁇ -gal activity is detected in most senescent settings, both in vitro and in vivo, it is considered a de facto hallmark of senescence.
  • Selective elimination of senescent cells may be determined by measuring a viability ratio of senescent cells versus proliferating cells, when populations of the respective cell types are each incubated with a fixed concentration of a test compound in
  • Compounds may be determined as capable of selectively eliminating senescent cells if the calculated viability ratio of the senescent cells versus the proliferating cells is lower than 0.9, preferably lower than 0.75.
  • Selective elimination of senescent cells may also be determined by incubating populations of senescent cells and proliferating cells respectively with various concentrations of a test compound in a suitable medium and measuring the LD50 value in each case (i.e. the concentration of the compound required to kill 50% of the cells in the respective population).
  • Compounds may be determined as capable of selectively eliminating senescent cells if the LD50 of the compound in proliferating cells is at least 2 times higher, preferably at least 3 times higher, than the LD50 of the compound in senescent cells.
  • skin cells may refer to any skin resident cell type (such as dermal fibroblasts, melanocytes and epidermal keratinocytes), or cell types from skin appendages (such as sebocytes), or a mixture thereof.
  • skin resident cell type such as dermal fibroblasts, melanocytes and epidermal keratinocytes
  • cell types from skin appendages such as sebocytes
  • sebocytes a mixture thereof.
  • the term refers to dermal fibroblasts, especially dermal papillary fibroblasts.
  • the one or more indole compounds of general formula (I) can be used perse or formulated with other ingredients to make a topical cosmetic or dermatological composition.
  • Topical compositions comprising the one or more indole compounds of general formula (I) for use in the invention can be formulated in a variety of forms for topical application, and will generally contain from about 0.01% to about 10%, preferably from about 0.1% to 1% by weight of the one or more indole compounds of general formula (I).
  • Topical compositions for use in the invention are preferably cosmetic in nature and will generally include a cosmetically acceptable vehicle.
  • Cosmetically acceptable means that the vehicle is suitable for topical application to the skin, has good aesthetic properties, is compatible with the one or more indole compounds of general formula (I) and any other ingredients, and will not cause any safety or toxicity concerns.
  • the vehicle may comprise an aqueous phase, an oil phase, an alcohol, a silicone phase or a mixture thereof, and may be in the form of an emulsion.
  • Emulsions can have a range of consistencies including thin lotions (which may also be suitable for spray or aerosol delivery), creamy lotions, light creams and heavy creams.
  • Exemplary emulsions include water-in-oil emulsions, oil-in-water emulsions, silicone-in-water emulsions, water-in-silicone emulsions, polyol-in-silicone emulsions, silicone-in-polyol emulsions, polyol-in-oil emulsions, oil-in-polyol emulsions, wax-in-water emulsions and water-oil-water triple emulsions.
  • Preferred emulsions include oil-in-water emulsions and water-in-oil emulsions.
  • Topical cosmetic compositions in the form of an emulsion, and suitable for use in the invention typically have an oil phase containing at one or more cosmetically acceptable fatty materials which may be liquid or solid at room temperature (25°C).
  • Suitable cosmetically acceptable fatty materials include naturally derived oils (such as sunflower oil, borage oil, soybean oil, castor oil, olive oil and almond oil); esters of monoalcohols or of polyols with monocarboxylic or polycarboxylic acids, at least one of the alcohols and/or acids comprising at least one hydrocarbon-based chain containing at least 6 carbon atoms (such as octyl palmitate, isopropyl myristate, isopropyl palmitate, isopropyl isostearate, hexyl laurate, isohexyl laurate, isohexyl palmitate, decyl oleate, isodecyl oleate, hexadecyl stearate, decyl stearate, dihexyldecyl adipate, lauryl lactate, myristyl lactate, cetyl lactate, oleyl stearate, oleyl ole
  • Topical cosmetic compositions in the form of an emulsion, and suitable for use in the invention typically have an aqueous phase, which may also include one or more organic liquids that are miscible with water at room temperature (25°C).
  • exemplary water-miscible organic liquids include monohydric and polyhydric alcohols and derivatives thereof such as C2-C 6 alkanols (such as ethanol and isopropanol); C2-C1 0 glycols and polyols (such as glycerol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol, dipropylene glycol, and diethylene glycol); C 3 -C1 6 glycol ethers (such as mono-, di-, or tripropylene glycol (C1-C4) alkyl ethers and mono-, di-, or triethylene glycol (C1-C4) alkyl ethers) and polyethylene glycol having 2 to 12 oxyethylene
  • Topical cosmetic compositions in the form of an emulsion, and suitable for use in the invention generally include surface active ingredients, such as emulsifiers and solubilizers, to enable two or more immiscible components to be combined homogeneously and to help stabilize the composition.
  • surface active ingredients such as emulsifiers and solubilizers
  • Emulsifiers that may be used to form O/Wor W/O emulsions include sorbitan oleate, sorbitan sesquioleate, sorbitan isostearate, sorbitan trioleate, PEG- 20 sorbitan isostearate, polyglyceryl-3-diisostearate, polyglycerol esters of oleic/isostearic acid, polyglyceryl-6 hexaricinolate, polyglyceryl-4-oleate, polyglyceryl-4 oleate/PEG-8 propylene glycol cocoate, polyglyceryl-2 dipolyhydroxystearate, PEG-30 dipolyhydroxystearate, oleamide DEA, TEA myristate, TEA stearate, magnesium stearate, sodium stearate, potassium laurate, potassium ricinoleate, sodium cocoate, sodium tallowate, potassium castorate, sodium oleate, cetyl phosphate,
  • Topical cosmetic compositions for use in the invention may also be formulated in a single phase carrier such as water and/or one or more water miscible organic liquids (such as the monohydric and polyhydric alcohols and derivatives thereof described above).
  • a single phase carrier such as water and/or one or more water miscible organic liquids (such as the monohydric and polyhydric alcohols and derivatives thereof described above).
  • Topical cosmetic compositions for use in the invention may also be formulated in solid forms such as gels or sticks.
  • a topical cosmetic composition for use in the invention may include additional skin care actives (for improving the physical and/or aesthetic characteristics of the skin).
  • additional skin care actives which are suitable for use in the invention include vitamins, minerals and/or antioxidants, emollients, humectants, skin lightening agents, sunscreens, anti-irritants, exfoliating agents and mixtures thereof.
  • Vitamins, minerals and/or antioxidants suitable for use in the invention include natural botanical antioxidants derived from plant materials such as fruits, vegetables, herbs and spices (such as goji berry, white tea, rosemary, green tea, grape seed and lemongrass extracts); vitamin A and its precursors or derivatives (such as beta-carotene, retinyl palmitate); vitamin B3 and its precursors or derivatives (such as niacinamide); vitamin B5 and its precursors or derivatives (such as panthenol and its precursors or derivatives); vitamin C and its precursors or derivatives (such as tetrahexyldecyl ascorbate, ascorbyl palmitate); vitamin E and its precursors or derivatives (such as d-alpha-tocopherol, tocopheryl acetate); vitamin K and its precursors or derivatives; selenium and its derivatives (such as L-selenomethionine); and alpha lipoic acid.
  • natural botanical antioxidants derived from plant materials such as fruits, vegetables,
  • Emollients suitable for use in the invention act to increase and maintain moisture in the skin by providing a protective coating to impede epidermal water loss.
  • emollients include diesters having at least one Cs-22 fatty chain (such as dibutyl adipate, diethyl sebacate, diisopropyl dimerate, and dioctyl succinate); branched chain esters having at least one Cs-22 fatty chain (such as 2-ethylhexyl myristate, isopropyl stearate and isostearyl palmitate); tribasic acid esters having at least one Cs-22 fatty chain (such as triisopropyl trilinoleate and trilauryl citrate), straight chain esters having at least one Cs-22 fatty chain (such as lauryl palmitate, myristyl lactate, and stearyl oleate); C10-20 fatty alcohols and acids (such as cetyl, myristyl, palmitic and
  • Humectants suitable for use in the invention act to increase and maintain moisture in the skin by attracting water to the stratum corneum of the epidermis.
  • humectants include amino acids, chondroitin sulfate, glycerin, diglycerin, triglycerin, polyglycerin, polypropylene glycol, polyethylene glycol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, 1,3-butylene glycol, 1,4- butylene glycol, ethylene glycol monoalkyl ether, diethylene glycol monoalkyl ether, erythritol, fructose, glucose, maltose, sucrose, lactose, xylose, inositol, lactitol, xylitol, sorbitol, mannitol, maltitol, panthenol, pentaeryth
  • Skin lightening agents suitable for use in the invention act to reduce total melanin content in skin, typically by inhibiting the function and activity of tyrosinase which plays an important role in the biosynthesis of melanin.
  • skin lightening agents include natural botanical skin lightening agents derived from plant materials (such as Arctostaphylos patula and Arctostaphylos viscida extracts, Emblica officinalis extract, Mitracarpus scaber extract, Uva ursi (bearberry) extract, Morns bombycis (mulberry) extract, Morns alba (white mulberry) extract, Broussonetia papyrifera (paper mulberry) extract, licorice extract, acerola cherry extract, Chlorella vulgaris extract, Aloe ferrox extract and Rumex occidentalis extract); synthetic or natural sugar amines (such as glucosamine, N-acetyl glucosamine, glucosamine sulfate, mannosamine, N-
  • Sunscreens suitable for use in the invention protect the skin from ultraviolet (UV) solar radiation falling within both the UVB region (between 290nm to 320 nm wavelengths) and the UVA region (between 320nm and 400nm wavelengths).
  • sunscreens include methoxycinnamate derivatives (such as octyl methoxycinnamate and isoamyl methoxycinnamate); camphor derivatives (such as 4-methyl benzylidene camphor, camphor benzalkonium methosulfate, and terephthalylidene dicamphor sulfonic acid); salicylate derivatives (such as octyl salicylate and homosalate); sulfonic acid derivatives (such as phenylbenzimidazole sulfonic acid); benzone derivatives (such as dioxybenzone, sulisobenzone, and oxybenzone); benzoic acid derivatives (such as aminobenzoic acid and octyld
  • Anti-irritants suitable for use in the invention include allantoin, aloe vera, a-bisabolol, caffeine, chamomile extract, Cola nitada extract, cucumber extract, dipotassium glycyrrhizinate, glycyrrhizic acid, green tea extract, lecithin or hydrogenated lecithin, licorice extract, tea tree oil, salicylic acid, acetylsalicylic acid, strontium acetate, strontium chloride, strontium nitrate, fatty acids with anti-irritant properties (such as linoleic acid and linolenic acid) and aromatic aldehydes with anti-irritant properties (such as 4-methoxy benzaldehyde, 4-ethoxy benzaldehyde, 4-butoxy benzaldehyde and 4-pentoxy benzaldehyde).
  • Exfoliating agents suitable for use in the invention include benzoyl peroxide, benzoic acid, 3- hydroxy benzoic acid, salicylic acid, acetic acid, trichloroacetic acid, 1-pyrrolidone-5- carboxylic acid, a-hydroxy acids (such as glycolic acid, lactic acid, malic acid, tartaric acid, and citric acid); b-hydroxy acids (such as b-hydroxybutyric acid); a-keto acids (such as pyruvic acid, 2-oxopropanoic acid, 2-oxobutanoic acid and 2-oxopentanoic acid); and oxa acids (such as 3,6,9-trioxaundecanedioic acid).
  • a-hydroxy acids such as glycolic acid, lactic acid, malic acid, tartaric acid, and citric acid
  • b-hydroxy acids such as b-hydroxybutyric acid
  • a-keto acids such as pyruvic acid, 2-oxopropanoic
  • a topical cosmetic composition for use in the invention may include additional functional ingredients (for improving the physical and/or aesthetic characteristics of the composition).
  • water soluble or colloidally water soluble polymeric thickening agents such as hydroxyethyl cellulose, methyl cellulose, hydroxypropyl methyl cellulose, polyquaternium-10, carrageenan, guar gum, hydroxypropyl guar gum, xanthan gum, polyvinylalcohol, acrylic acid/ethyl acrylate copolymers, carboxyvinyl polymers, cross-linked polyacrylate polymers and polyacrylamide polymers
  • structurant clays such as magnesium aluminum silicate, attapulgite, bentonite, montmorillonite and hectorite
  • inorganic pigments such as titanium oxide, zirconium oxide, cerium oxide zinc oxide, iron oxide, chromium oxide and ferric blue
  • organic pigments such as carbon black and barium, strontium, calcium, and aluminium lakes
  • pearlescent agents such as mica coated with titanium oxide and/or iron oxide
  • dyes, preservatives such as hydroxyethyl cellulose, methyl
  • a topical cosmetic composition for use in the invention may be packaged in a suitable container to suit its viscosity and intended use by the consumer.
  • a lotion or a cream can be packaged in a bottle or a roll-ball applicator, or a propellant-driven aerosol device or a container fitted with a pump suitable for finger operation.
  • the composition When the composition is a cream, it can simply be stored in a non-deformable bottle or squeeze container, such as a tube or a lidded jar.
  • the composition is suitably applied to the skin, preferably facial skin, at the rate of one or two applications per day. Generally, an amount corresponding to about 1 to 2 ml of the composition per application is applied uniformly over the area of treatment twice daily for a period of at least 7 (seven) days, more preferably at least 30 (thirty) days.
  • a high-throughput compound screen of 1240 test compounds including inter alia 1-indoleacetic acid (lUPAC: 2-indol-1-ylacetic acid was optimised in primary adult human dermal fibroblasts (HDFs). For this, a model of replicative senescence in HDFs was established. In brief, early proliferating (EP) fibroblasts at passage 11 were serially passaged until they reached replicative senescence at passage 29. Deeply senescent (DS) fibroblasts were then defined as a population which did not expand when kept in culture for three weeks post-replicative senescence.
  • EP early proliferating
  • DS Deeply senescent
  • Actinomycin D a drug widely reported to induce apoptosis in multiple cell types, was optimised for use as a positive ‘senolytic control’ for the high-throughput compound screen in EP (0.02mM) and DS (0.2mM) HDFs.
  • P7 and P39+1 HDFs were thawed, passaged or kept in culture, respectively, and manually seeded at P9 (EP) or P39+3 (DS) into 384-well plate format on day fourteen.
  • a liquid handling robot added test compounds to the cells at three serial concentrations.
  • the negative DMSO vehicle control and Actinomycin D positive control (0.02mM for EP HDFs and 0.2mM for DS HDFs) were manually added to each plate. Subsequently, cells were incubated with the test compounds for 48 hours before media changing on day seventeen.
  • 1-indoleacetic acid according to the invention was defined as ‘senolytic’ for at least one concentration of the three serial concentrations in the EP and DS HDFs.
  • 1-indoleacetic acid according to the invention demonstrates a preferential cytotoxicity for senescent cells, compared to growing cells.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne l'utilisation d'un ou de plusieurs composés d'indole correspondant à la formule générale (I), dans laquelle Z est un radical hydrocarboné aliphatique divalent et M est un atome d'hydrogène ou un cation formant un sel; pour le traitement de signes du vieillissement de la peau.
PCT/EP2021/064082 2020-06-19 2021-05-26 Utilisation de composés d'indole pour traiter les signes du vieillissement de la peau WO2021254751A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP21728239.1A EP4168130A1 (fr) 2020-06-19 2021-05-26 Utilisation de composés d'indole pour traiter les signes du vieillissement de la peau

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP20181081.9 2020-06-19
EP20181081 2020-06-19

Publications (1)

Publication Number Publication Date
WO2021254751A1 true WO2021254751A1 (fr) 2021-12-23

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010066351A1 (fr) * 2008-12-09 2010-06-17 Cognis Ip Management Gmbh Blanchiment de la peau
WO2020084105A2 (fr) * 2018-10-25 2020-04-30 Universität Für Bodenkultur Wien Compositions pour l'élimination de cellules sénescentes

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010066351A1 (fr) * 2008-12-09 2010-06-17 Cognis Ip Management Gmbh Blanchiment de la peau
WO2020084105A2 (fr) * 2018-10-25 2020-04-30 Universität Für Bodenkultur Wien Compositions pour l'élimination de cellules sénescentes

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
THOMAS E. D'AMBRA ET AL: "Conformationally restrained analogs of pravadoline: nanomolar potent, enantioselective, (aminoalkyl)indole agonists of the cannabinoid receptor", JOURNAL OF MEDICINAL CHEMISTRY, vol. 35, no. 1, 1 January 1992 (1992-01-01), US, pages 124 - 135, XP055738277, ISSN: 0022-2623, DOI: 10.1021/jm00079a016 *

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